A pot, atom and step economy (PASE) synthesis of new 5-C substituted 2,4-diamino-5H-chromeno [2,3-b]pyridine-3-carbonitriles was carried out. This process involves the one-pot, pseudo four-component reaction of salicylaldehydes, malononitrile, 1,3-cyclohexanediones and Et 3 N as a catalyst in acetonitrile at reflux. This novel one-pot reaction provides an effective and convenient way to 5-C cyclohexyl-functionalized chromeno[2,3b]pyridines, which are promising compounds for different biomedical applications. The procedure utilizes readily available reagents, it is easily carried out and the work up is not complicated. 2,4-diamino-5-(2-hydroxy-6-oxocyclohex-1-en-1yl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles are crystallized directly from the reaction mixture and the isolation includes only filtration. Molecular docking studies of the synthesized 2,4diamino-5H-chromeno[2,3-b]pyridine-3-carbonitriles were also carried out to elucidate their relationship with the binding pockets of the mitogen activated protein kinase (MK).
A new multicomponent reaction is reported: the one‐pot transformation of salicylaldehydes, 2‐aminoprop‐1‐ene‐1,1,3‐tricarbonitrile (malononitrile dimer), and trialkylphosphites results in the efficient formation of (2,4‐diamino‐3‐cyano‐5H‐chromeno[2,3‐b]pyridin‐5‐yl)phosphonates. The scope of this one‐pot reaction was investigated. The isolation of substituted phosphonates is very easy. The optimized reaction conditions and a mechanistic rationale for the complex multicomponent transformation are presented. This facile PASE approach offers a powerful tool for the selective formation of new types of functionalized 5‐P‐substituted 2,4‐diamino‐5H‐chromeno[2,3‐b]pyridine scaffolds containing the phosphonate fragment, which are promising compounds for various biomedical applications, among them the treatment of human inflammatory diseases and cancer therapy.
A highly diastereoselective three-component cascade reaction among aromatic aldehydes, 3-arylisoxazol-5(4H)-ones and 3-aminocyclohex-2-en-1-ones takes place under the catalysis of triethylamine, providing (3SR,4SR)-4-aryl-3-[(E)-(hydroxyimino)(aryl)methyl]-4,6,7,8-tetrahydroquinoline-2,5(1H,3H)-diones in 45-85% yields. The transformation presumably proceeds through a sequential cascade of Knoevenagel/Michael-addition/cyclization/ring-opening reactions. This process was carried out in green media (EtOH/water, 1:1-1:3) at reflux. Products are crystallized directly from the reaction mixture and their isolation includes only filtration. The structure of (3SR,4SR)-3-[(E)-(hydroxyimino)(phenyl)methyl]-7,7-dimethyl-4-phenyl-4,6,7,8-tetrahydroquinoline-2,5(1H,3H)-dione was confirmed by X-ray diffraction analysis.
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